I've been told that vacancy rates in NY are around 5%, so I guess I should just deduct 5% from my monthly cash flow for that.My rent is currently 1400 a month, so if I can break even (which I would once rents go up to market rate) I'd be saving 1400 a month, so after around 3-4 years my initial downpayment + closing costs would be returned.

If the tenants pay the mortgage, and I have positive cash flow, it doesn't matter to me what rate I pay, as it is a deductible expense. 

[I'm comfortable with the RPE requirements and the accelerated depreciation process and cost, the only concern is AMT]ThanksDavideven if your are subject to AMT, it will not nullify your real estate deduction from depreciation.  

@Chris Henry If you do not want to build a rental portfolio, then I would recommend checking with your CPA to see what other expenses that you currently have that you can include as rental expenses (ie. make sure you're getting all the deductions your entitled to.) 

Some of my clients just gives me a call and they get the answer they need and pay me for my time, probably cheaper than a lunch or dinner plus it is tax deductible.

Homeowner deductions, annual income, cost of financing, and your own personal comfort level dealing with renters (or PMs) all play into it.

If the damage is near the cost of your deductible or lower, there isn't a point in filing a claim.

My goal would be to get the other guys carrier to pay so I don't lose the deductible and don't bring attention to a bad situation.

I feel HELOC offers flexibility and deduction benefits with less downside risk

Deductible: This is not a coverage but rather your portion of a claim.